Regioselective Copper-Catalyzed Amination of Bromobenzoic Acids Using Aliphatic and Aromatic Amines

Christian Wolf,* Shuanglong Liu, Xuefeng Mei, Adam T. August, and Michael D. Casimir
Department of Chemistry, Georgetown University, Washington, D.C. 20057 cw27@georgetown.edu
J. Org. Chem., 2006, 71 (8), pp 3270–3273
DOI: 10.1021/jo060034a
Publication Date (Web): March 22, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

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A chemo- and regioselective copper-catalyzed cross-coupling procedure for amination of 2-bromobenzoic acids is described. The method eliminates the need for acid protection and produces N-aryl and N-alkyl anthranilic acid derivatives in up to 99% yield. N-(1-Pyrene)anthranilic acid has been employed in metal ion-selective fluorosensing. Titration experiments showed that this pyrene-derived amino acid forms an equimolar complex with Hg(II) in water resulting in selective fluorescence quenching even in the presence of other metal ions such as Zn(II) and Cd(II).

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  • Published In Issue April 14, 2006
  • Received January 6, 2006

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